JP4911925B2 - Anti-termite agent - Google Patents

Description

  The present invention relates to an anti-termite agent (termite control agent) containing an imidazole compound and having high safety and controllability.

  Termites damage and destroy wooden structures such as wooden buildings and cables buried underground. As such termite control agents, organochlorine compounds, organophosphorus compounds, carbamate compounds, and pyrethroid compounds have been used, but it has been difficult to satisfy both safety and control properties. It was.

Further, it is known that pyrazole compounds and triazine compounds also have a termite control effect and a food poisoning effect. For example, JP-T-2001-504823 (Patent Document 1) discloses a method for protecting a building in which an insecticidal effective amount of a compound is sprayed at a discontinuous position around or under the building. It is disclosed that it is an insecticide (1-arylpyrazole type insecticide) that can kill termites in the nest when the termites are brought back to the nest. Japanese Patent Laid-Open No. 2003-81716 (Patent Document 2) discloses a termite food poison containing a specific triazine compound as an active ingredient. However, even with such termite control agents or food poisons, the termite control effect is still insufficient.
JP-T-2001-504823 (Claims 1, 5 and 6) JP 2003-81716 A (Claim 1)

  Accordingly, an object of the present invention is to provide an anti-termite agent that has an excellent termite control effect and is highly safe.

  As a result of intensive studies to achieve the above-mentioned problems, the present inventors have found that a specific imidazole compound has a high safety and an excellent termite control effect, and completed the present invention.

  That is, the anti-termite agent of the present invention contains an imidazole compound, for example, an imidazole compound represented by the following formula (1).

(Wherein R ¹ , R ² , R ³ and R ⁴ are the same or different and represent a hydrogen atom, an amino group, a nitro group, a hydroxyl group, or a hydrocarbon group which may have a substituent)
The following anti-termite agents are also included in the present invention.
(i) The anti-termite agent, wherein, in the formula (1), the hydrocarbon group is a hydrocarbon group having 1 to 16 carbon atoms.
(ii) The anti-termite agent, wherein, in the formula (1), the hydrocarbon group is an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group or an aralkyl group.
(iii) The anti-termite agent, wherein R ² is an alkyl group and R ¹ , R ³ and R ⁴ are hydrogen atoms in the formula (1).
(iv) The anti-termite agent, wherein, in the formula (1), R ² is an aryl group, R ³ is an alkyl group, and R ¹ and R ⁴ are hydrogen atoms.
(v) The anti-termite agent used for treating xylem or soil.
(vi) The anti-termite agent used as a bait agent.

The present invention also includes a method for controlling or preventing termites by applying the anti-termite agent to a treatment area or a treatment object that can be harmed by termites. Further, the present invention includes the following termite control or prevention methods.
(i) The said control or prevention method which applies the said anti- termite agent to the to-be-processed object selected from soil and wood.
(ii) The said control or prevention method which makes the said termite agent contact or ingest with respect to a termite.

  In this specification, the term “control or prevention” of termites refers to the prevention, or prevention of termite reproduction, development, colonization, etc., due to extermination or weakening of termites, repellent effects, etc. ) Means.

  In this invention, since an anti-termite agent is comprised with the specific imidazole compound, it is excellent in the termite control effect and can provide a highly safe anti-termite agent. When such an anti-termite agent is used, a high termite control effect can be obtained by contacting and / or feeding the termite. Moreover, the damage of the to-be-processed object can be prevented by eating of the to-be-processed object being inhibited.

[Anti-termite agent]
The anti-termite agent of the present invention includes an imidazole compound, for example, a compound represented by the following formula (1).

(Wherein R ¹ , R ² , R ³ and R ⁴ are the same or different and represent a hydrogen atom, an amino group, a nitro group, a hydroxyl group, or a hydrocarbon group which may have a substituent)
In the formula (1), the hydrocarbon group (that is, the hydrocarbon group of the hydrocarbon group which may have a substituent) has, for example, 1 to 16, preferably 1 to 14 carbon atoms, Preferably about 1-10 hydrocarbon groups are mentioned. The hydrocarbon group may be either a saturated or unsaturated hydrocarbon group.

  Specific examples of the hydrocarbon group include an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, and an aralkyl group. Of these hydrocarbon groups, an alkyl group, an alkenyl group, or an aryl group is often used.

The alkyl group may be any of linear and branched alkyl groups such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, t-butyl, n-pentyl, isopentyl, hexyl, Examples include heptyl, octyl, nonyl, decyl, undecyl, dodecyl (for example, C _1-10 alkyl group and the like). Of these alkyl groups, C _1-6 alkyl groups, particularly C _1-4 alkyl groups are preferred.

The alkenyl group may be any of linear and branched alkenyl groups, and examples thereof include vinyl, allyl, isopropenyl, butenyl, butadienyl, methallyl, butenyl, hexenyl, octenyl (for example, C _{2 -10} alkenyl group, etc.). Of these alkenyl groups, C _2-6 alkenyl groups (particularly vinyl and allyl groups) are preferred.

Examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexyl, cyclooctyl, and cyclononyl (eg, a C _3-9 cycloalkyl group). Of these cycloalkyl groups, a C _3-8 cycloalkyl group, particularly a C _3-6 cycloalkyl group is preferred.

Examples of the aryl group include C _6-14 aryl groups such as phenyl group, naphthyl group, anthryl group, phenanthryl group, and azulenyl group; C _1-4 alkyl-C _6-14 such as tolyl group and xylyl group. An aryl group; a C _6-10 aryl-C _6-14 aryl group such as a biphenylyl group; a (C _6-10 aryl-C _1-4 alkyl) C _6-14 aryl group such as a _benzylphenyl group. Of these aryl groups, a C _6-12 aryl group, a C _1-3 alkyl-C _6-12 aryl group, particularly a C _6-10 aryl group (such as a phenyl group) is preferable.

Examples of the aralkyl group include aralkyl groups having about 7 to 16 carbon atoms such as benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl and diphenylmethyl. Among these aralkyl groups, a C _6-10 aryl-C _1-4 alkyl group (for example, a C _6-10 aryl-C _1-2 alkyl group), particularly a benzyl group is preferable.

Examples of the substituent that the hydrocarbon group may have include a hydroxyl group and a C _1-6 alkoxy group [for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentyloxy, hexyloxy (preferably Is a C _1-3 alkoxy group)], C _2-6 acyloxy group [acetyloxy group, ethylcarbonyloxy, propylcarbonyloxy (preferably C _2-4 acyloxy group)], amino group, C _1-3 alkyl amino group [e.g., a C _1-3 alkyl group, methyl, ethyl, having a propyl group N- mono C _1-3 alkylamino group and N, N- di C _1-3 alkylamino group, etc.], a nitro group , carboxyl group, C _1-4 alkoxy - carbonyl group (methoxycarbonyl group, an ethoxycarbonyl group), C Gen atom (chlorine, bromine, fluorine, iodine atom) and the like. Of these substituents, a hydroxyl group, the alkoxy group, a halogen atom, and the like are preferable.

  The hydrocarbon group may have one or more of these substituents. The number of substituents is, for example, 1 to 3, preferably 1 or 2, with respect to one hydrocarbon group. When the hydrocarbon group has a plurality of substituents, the type of the substituent may be the same or different.

Of the hydrocarbon groups which may have a substituent, an alkyl group (such as a C _1-4 alkyl group), a hydroxyalkyl group (such as a hydroxy C _1-4 alkyl group such as a hydroxyethyl group), an alkenyl group (C _2-5 alkenyl groups), aryl groups (C _6-10 aryl groups, etc.), aralkyl groups (C _6-10 aryl-C _1-2 alkyl groups, etc.) and the like are preferable.

In the above formula (1), the group represented by R ¹ is preferably, for example, a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkenyl group, or an aralkyl group. The group represented by R ² is preferably, for example, a hydrogen atom, an amino group, a nitro group, an alkyl group, or an aryl group. As the group represented by R ³ , for example, a nitro group, an alkyl group, or a hydroxyalkyl group is preferable. Examples of the group represented by R ⁴ include a C _1-4 alkyl group and a hydrogen atom (particularly a hydrogen atom).

A preferred imidazole compound is a hydrocarbon group (substituted or unsubstituted) in which at least one of R ^{1 to} R ³ (that is, the 1-position, 2-position and 4-position of the imidazole ring) may have a substituent. Substituted hydrocarbon group). In such a compound, R ⁴ (position 5) may be a hydrogen atom. Incidentally, imidazole compounds, among R ¹ to R ^3, 2 two (e.g., R ¹ and R ³ (1,4-positions), R ¹ and R ² (1,2-position), R ² and R ³ (2,4-position)) may be a substituted or unsubstituted hydrocarbon group.

Preferred combinations of R ^{1 to} R ⁴ include the following combinations (i) to (iii).

(i) R ¹ (position 1): substituted or unsubstituted hydrocarbon group (for example, alkyl group, hydroxyalkyl group, alkenyl group, aryl group, aralkyl group), R ² (position 2): hydrogen atom or alkyl group, R ³ (4th position) and R ⁴ (5th position): hydrogen atom
(ii) R ¹ (1-position): hydrogen atom, R ² (2-position): substituted or unsubstituted hydrocarbon group (for example, alkyl group, aryl group), R ³ (4-position): hydrogen atom or alkyl group, R ⁴ (position 5): hydrogen atom
(iii) R ¹ (1-position): hydrogen atom, R ² (2-position): hydrogen atom, R ³ (4-position): substituted or unsubstituted hydrocarbon group (for example, alkyl group, hydroxyalkyl group, aryl group, Aralkyl group), R ⁴ (position 5): hydrogen atom Among these, in the combination of (ii) above, particularly in the formula (1), R ² is an alkyl group, and R ¹ , R ³ and R ⁴ are Imidazole compounds that are hydrogen atoms (2-C _1-4 alkylimidazoles such as 2-methylimidazole), R ² is an aryl group, R ³ is an alkyl group, and R ¹ and R ⁴ are hydrogen atoms Imidazole compounds (such as 2-C _6-10 aryl-4-C _1-4 alkyl-imidazole such as 2-phenyl-4-methylimidazole) and the like are preferable.

  As the imidazole compound represented by the formula (1), a known compound (for example, a commercially available product) may be used, or a compound synthesized according to a conventional method may be used. For example, in imidazole compounds other than imidazole (substituted imidazole compounds and the like), for example, imidazole has an amino group, a nitro group, a hydroxyl group, or a hydrocarbon group which may have a substituent, a conventional functional group. According to the introduction method, it may be produced by introduction.

  The anti-termite agent of the present invention is not particularly limited as long as it contains the imidazole compound as an active ingredient, and may be composed of the imidazole compound alone, as long as the characteristics of the imidazole compound are not impaired. The composition comprised by these components may be sufficient. As other components, other active ingredients (other termite control ingredients, antibacterial ingredients (antiseptic and fungicide), etc.), carriers (or bases), additives and the like can be used.

  The content of the imidazole compound in the anti-termite agent may be appropriately selected according to the use and dosage form, and is not particularly limited. For example, 0.01 to 100% by weight, preferably 0.1 to 90% by weight, More preferably, it is about 1 to 50% by weight (particularly 2 to 30% by weight). In the liquid anti-termite agent (liquid agent), the ratio of the imidazole compound can be selected from the range of, for example, about 0.001 to 90% by weight, preferably 0.001 to 30% by weight, and more preferably 0.005 to 0.005%. It may be about 0.01 to 20% by weight (particularly 0.05 to 10% by weight).

  The other termite-controlling component may be a synthetic or natural product and may be a conventional termite-controlling component such as an organic phosphorus compound (such as phoxime, chlorpyrifos, fenitrothion, pyridafenthion, isofenphos), carbamate-based Compounds (bassa, propoxer, etc.), pyrethroid compounds (cyfluthrin, permethrin, tralomethrin, fenpalarelate, etofenprox, bifenthrin, ciphenothrin, silafluophene, pyrethrin, praretrin, etc.), neonicotinoid compounds (nitenpyram, acetamiprid, clothianidin) , Imidacloprid, thiamethoxam, etc.), phenylpyrazole compounds (such as fipronil), pyrrole compounds (such as chlorfenapyr), nereistoxin Products (such as bensultap), amidinohydrazone compounds (such as hydramethylnon), semicarbazone compounds, higher alcohols (such as tridecanol and hexadecanol), boric acids such as orthoboric acid, chitin synthesis inhibitors (rufenuron, hexaflumuuron) , Diflubenzuron, flufenoxuron, etc.), juvenile hormone-like compounds (methoprene, hydroprene, etc.), fatty acids (decanoic acid, octanoic acid, etc.), hiba oil, hiba neutral oil and the like. These other termite control components can be used alone or in combination of two or more.

  The ratio of the other termite control component can be selected from a ratio of about 0 to 100 parts by weight with respect to 100 parts by weight of the imidazole compound, for example, 0.1 to 80 parts by weight, preferably about 1 to 50 parts by weight. is there.

Examples of the antibacterial component include organic iodine compounds (3-bromo-2,3-diiodo-2-propenylethyl carbonate, 3-iodo-2-propynylbutylcarbamate (IPBC), 2,3,3-triiodo Allyl alcohol, parachlorophenyl-3-iodopropargyl formal, etc.), benzimidazole and benzothiazole compounds [2- (4-thiazolyl) benzimidazole, 2-thiocyanomethylthiobenzothiazole etc.], triazole compounds [1- (2 -(2 ', 4'-dichlorophenyl) -1,3-dioxolan-2-ylmethyl) -1H-1,2,4-triazole, 1- (2- (2,4-dichlorophenyl) -4-propyl-1 , 3-Dioxolan-2-ylmethyl) -1H-1,2,4-tri Zole (generic name: propiconazole), α- (2- (4-chlorophenyl) ethyl) -α- (1,1-dimethylethyl) -1H-1,2,4-triazole-1-ethanol (generic name) : Tebuconazole, etc.], natural products [4-isopropyltropolone (hinokitiol), borax, etc.], antibacterial metals [silver compounds (for example, metallic silver; silver halides such as AgCl, AgF, AgF ₂ ; Ag ₂ O, Oxides such as AgO; sulfides such as Ag ₂ S; oxyacid salts such as Ag ₂ SO ₄ , Ag ₂ CrO ₄ , Ag ₃ PO ₄ , Ag ₂ CO ₃ and Ag ₂ SiO ₃ ), copper compounds, zinc Compound etc.]. These antibacterial components can be used alone or in combination of two or more.

  The proportion of these antibacterial components can be selected from a proportion of about 0 to 2000 parts by weight with respect to 100 parts by weight of the imidazole compound, and is, for example, about 50 to 1000 parts by weight, preferably about 100 to 500 parts by weight.

  The carrier (or base) can be appropriately selected according to the dosage form of the anti-termite agent (the dosage form described later), and may be any of aqueous and oily carriers such as liquid carriers [silicone oil, Oily carriers such as animal fats and oils, vegetable fats and oils (for example, rapeseed oil); aqueous solvents, organic solvents, etc.], gel carriers (alginic acids, cellulose or derivatives thereof, polyethylene glycol, etc.), solid or semi-solid carriers [powdered form Carriers {Various carriers frequently used for agricultural chemicals, horticultural preparations, etc., for example, clay minerals (zeolite, sepiolite, attapulgite (palygorskite), etc.), synthetic zeolite, charcoal (charcoal, bamboo charcoal, etc.), talc (talc powder, wax Stone powder, etc.), clays (fine powder clay, etc.), pumices (rhyolite natural glass, perlite (manufactured by Neolite Kosan Co., Ltd.)) Other than mineral powders (silica sand, vermiculite, mica, calcium carbonate, etc.), metal oxides (titanium oxide, etc.), sulfur powder, urea powder, vegetable powders (peat moss, wood powder, starch, etc.); Sugars such as starch and dextrin (polysaccharides and the like); Synthetic polymers such as carboxyvinyl polymer and cross-linked polyvinyl pyrrolidone; Cellulose ethers; Metal soaps and the like}, Resins with film-form performance, wax, solid paraffin, long chain fatty acids Ester, higher alcohol, higher fatty acid, etc.)] and the like. The carriers may be used alone or in combination of two or more.

  Among the liquid carriers, aqueous or organic solvents include water, alcohols [trade name: ISOFOL 14 (manufactured by Condea Japan Co., Ltd.); lower aliphatic alcohols such as ethanol and isopropanol; ethylene glycol and diethylene glycol ( Poly) alkylene glycol; aliphatic polyhydric alcohols such as glycerin], ethers (chain ethers such as diethyl ether; cyclic ethers such as tetrahydrofuran; carbitols such as carbitol and diethylene glycol dimethyl ether), ketones ( Acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), cellosolves (alkyl cellosolve, such as methyl cellosolve), esters (ethyl acetate, fatty acid esters such as diisononyl adipate, etc.) Etc.)), hydrocarbons [hydrocarbon solvents based on naphthene (trade name: Naphthezol 240 (manufactured by Nippon Petrochemical Co., Ltd.)); aliphatic hydrocarbons such as hexane; alicyclic rings such as cyclohexane Formula hydrocarbons: Toluene, xylene, trade name: Nisseki Hyzol SAS-310 (manufactured by Shin Nippon Petrochemical Co., Ltd.), etc .; halogenated hydrocarbons such as methylene chloride, chloroform, etc.], amides (Dimethylformamide etc.), nitriles (acetonitrile etc.), sulfoxides (dimethylsulfoxide etc.) etc. are mentioned. These solvents can be used alone or in combination of two or more. Of these solvents, water or water-soluble organic solvents (lower aliphatic alcohols, (poly) alkylene glycols, aliphatic polyhydric alcohols, acetone, etc.) are often used. Among the solvents, a highly volatile solvent (for example, a lower alcohol such as ethanol, acetone, acetonitrile, short chain ether, etc.) may be used.

  Examples of the additive used for the anti-termite agent include conventional additives such as emulsifiers [for example, various surfactants such as anionic, cationic, nonionic, and amphoteric surfactants (particularly anionic or nonionic). Surfactants (for example, trade name: NAROACTY N-100 (manufactured by Sanyo Chemical Co., Ltd.)), etc.], thickener, pH adjuster, binder, stabilizer (antioxidant, ultraviolet absorber) Etc.), spreading agents, wetting agents, penetrating agents, flow aids, anti-caking agents, flocculants, drying agents, deodorants, coloring agents, and the like. These additives can be used alone or in combination of two or more.

  The anti-termite agent of the present invention can be used in any dosage form, such as a liquid agent (solution, wettable powder, suspension, dispersion, emulsion, oil, lotion, microcapsule, microsphere, Flowable agents, etc.), solid agents (powder, granules, tablets, foaming agents, etc.), semi-solid agents (paste agents, creams, etc.), sprays or aerosols. Moreover, according to these dosage forms, the said support | carrier and additive are selected suitably and used. For example, in the case of a liquid anti-termite agent (liquid agent) such as a solution or an emulsion, a liquid carrier such as the above-mentioned solvent, an emulsifier or surfactant, a pH adjuster, or the like may be used in combination.

  Further, the anti-termite agent may be used in a form in which the liquid anti-termite agent and an appropriate solid diluent (for example, the solid (powdered) carrier) are mixed and dried if necessary. A solid diluent can be used individually or in combination of 2 or more types. Among solid diluents, mineral powders such as talc and silica sand, and vegetable powders such as wood powder are widely used.

  In such a form, the ratio (weight ratio) between the solid diluent and the liquid agent is, for example, solid diluent / liquid agent = 100/1 to 1/5, preferably 50/1 to 1/3, and more preferably 30. / 1 to 1/2 (especially 10/1 to 1/1).

  The anti-termite agent of the present invention can be used as an area to be treated or an object to be treated (for example, xylem such as soil and / or wood, concrete, basic insulation, etc.) that can be harmed by termites (termites can grow or propagate). By applying, termites can be effectively controlled or prevented. The anti-termite agent may be applied to the object to be treated by, for example, mixing the anti-termite agent and the object to be treated in advance depending on the form of the object to be treated. You may apply by apply | coating. For example, anti-termite agents are applied directly to wood parts such as wood, anti-termite agents are treated on soil to prevent intrusion, a barrier layer is built, and wood is mixed or sprayed on basic insulation. It may be a method for indirectly preventing the damage to the body. In addition, the application method is aimed at bait treatment inside and outside the house, embedded in the soil, pasted on the damaged part, mixed with an anti-termite agent in the adhesive, plywood, laminated wood, The method may be applied to a wooden board or the like. Further, the anti-termite agent is prepared by applying, impregnating, kneading, etc. to a sheet or film-like substrate such as a synthetic resin sheet, paper, cloth, etc. to prepare a sheet agent. It is also possible to effectively act by placing or sticking on the entry point or the occurrence point of. The present invention includes a method for controlling or preventing such termites. The anti-termite agent of the present invention is particularly useful for use for treating soil, xylem and the like.

  When an anti-termite agent is used for soil treatment (when used as a soil treatment agent), it can be applied by spraying (for example, spraying on the soil surface, spraying on grooves formed in the soil), or mixing with soil. Termites can be applied to the soil. In such applications, the anti-termite agent is applied by spraying or mixing, so the form (or dosage form) of the anti-termite agent is a solid agent such as a powder or a granule, a liquid agent, a liquid agent and a granular carrier. It is preferable to use a mixture of The soil may contain silica sand and the like.

  Further, when an anti-termite agent is used for treating a xylem (used as a xylem treating agent), the anti-termite agent can be usually applied to the xylem by coating, impregnation, injection, spraying, or the like. Therefore, the form (or dosage form) of the anti-termite agent is a liquid agent (emulsion, an oil agent using the oily liquid carrier), a semi-solid agent, a spray (a liquid agent, a spray using a powder, etc.), etc. Also good. In addition, the anti-termite agent can be applied to a place where the termite is likely to harm, in particular, a place where a termite is likely to be generated or invaded, for example, a lower part of a water floor such as a kitchen, a bathroom, a toilet, a living room, It is preferably applied to wooden products such as floor corners, ceilings, foundations, pillars, walls, and furniture.

  In the anti-termite agent of the present invention, the termite can be killed or weakened effectively by bringing the termite agent into contact (attachment) with the termite, and as a result, a high termite control effect is obtained.

  The bait agent may be applied as the above-mentioned xylem treating agent in the form of a liquid agent, for example, but is usually in the form of a solid agent (powder, granule, tablet, etc.) or a semi-solid agent (paste agent, etc.) Therefore, it can be applied by arranging it in a place where termites easily pass. The bait preparation usually contains termite foods and termite favorite foods.

  Examples of termite foods or tastes include celluloses [eg, wood flour (such as pine wood flour), decayed wood, plant fine slices (such as sawdust, bark shreds], paper, etc.), sugars [simple Sugars (mannose, galactose, rhamnose, etc.), oligosaccharides (lactose, raffinose, etc.), sugar alcohols (mannitol, xylitol, etc.), cyclic sugar alcohols (inositol, etc.), polysaccharides (julan gum, xanthan gum, etc.), etc. Is mentioned. These termite foods or tastes can be used alone or in combination of two or more. Of these termite diets or tastes, pine wood flour, mannose, galactose, mannitol, duran gum and the like are preferred.

  The ratio of the termite food or the favorite food is, for example, about 0.1 to 1000 parts by weight, preferably 1 to 500 parts by weight, and more preferably about 5 to 200 parts by weight with respect to 100 parts by weight of the imidazole compound. Good.

  The anti-termite agent of the present invention can be applied to various termites to obtain a high control effect. Examples of such termites include insects belonging to the order of termites, such as insects belonging to the termite termites such as Yamato termites and termites, and insects belonging to the termite family such as American white termites and dicot termites .

  The anti-termite agent of the present invention has an excellent termite control effect and also has high safety. Therefore, it is useful as various termite control preparations applied to the treatment of soil and xylem. In particular, it is useful as a bait agent for controlling termites by contacting with termites or feeding them.

  Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not limited to these examples.

[Termite contact test]
0.1 g of imidazole compound was dissolved in acetone in a glass bottle, 10 g of silica sand was added to the solution and mixed, and further acetone was evaporated by air drying. Distilled water was added to and mixed with the resulting mixture so that the content of the distilled water was 8% by weight (optimum water content of termite activity). Ten termite ants were placed in a glass bottle, the number of dead termites was observed over time, and the termite control effect by contact was evaluated according to the following criteria.

◎: All heads die within 6 hours ○: All heads die within 3 days after 6 hours △: All heads die within 7 days after 3 days ×: Some termites die over 7 days XX: No ant killing effect.

[Filter paper test (termite food poisoning test)]
An acetone solution containing an imidazole compound at a concentration of 1 mg / mL was prepared, 40 μL of this acetone solution was dropped on a filter paper having a diameter of 12 mm, and air-dried to make acetone disappear. This treated filter paper was placed on silica sand (water content 8% by weight) filled in a glass bottle, and 50 termite ants were put into the glass bottle so as to be in contact with the filter paper. 21 days after the termite injection, the filter paper damage rate (%) was observed, and the effect of eating damage was evaluated according to the following criteria.

A: Filter paper damage rate is 0% or more and less than 20% B: Filter paper damage rate is 20% or more and less than 40% C: Filter paper damage rate is 40% or more and less than 60% D: Filter paper damage rate is 60% or more and less than 80% E: Filter paper damage rate is 80% or more and less than 100% F: Filter paper damage rate is 100%.

Example Using the imidazole compounds shown in Tables 1 and 2, the contact test and the food poisoning test were conducted. The results of the contact test are shown in Table 1, and the results of the food poisoning test are shown in Table 2. In addition, as a control, the results of tests conducted in the same manner as in the above test method except that no imidazole compound is used are also shown. In addition, all the imidazole compounds used the commercial item.

  As is clear from the table, in the examples using the imidazole compound, a high termite killing effect (termite control effect) was shown in the contact test and / or feeding (food poisoning) test. In particular, a strong ant killing effect was observed for imidazole compounds having an alkyl group at the 1st and 2nd positions. In addition, the imidazole compound having one methyl group had a particularly high feeding inhibitory effect. Furthermore, 2-phenyl-4-methylimidazole showed a very strong feeding inhibitory action.

Formulation Example-I
Oil for emulsification For soil (% is based on weight)
Diisononyl adipate 30%
Diethylene glycol monomethyl ether 34%
Rapeseed oil 10%
Narrow Acty N100 16%
2-phenyl-4-methylimidazole 10%
Total 100%
Preparation of emulsion for soil 30 parts by weight of diisononyl adipate, 34 parts by weight of diethylene glycol monomethyl ether, 10 parts by weight of rapeseed oil, 16 parts by weight of “Naroacty N100” (manufactured by Sanyo Chemical Co., Ltd.), 2-phenyl- An oil agent for emulsification is prepared by adding 10 parts by weight of 4-methylimidazole and dissolving it uniformly.

Formulation Example-II
Oil agent For wood (% is based on weight)
(i) (ii)
Diisononyl adipate 55% 55.9%
Diethylene glycol monomethyl ether 20% 20%
Naphthezol 240 20% 20%
Tebuconazole 1% 1%
Propiconazole 1% 1%
2-Phenyl-4-methylimidazole 3% 2%
Clothianidin-0.1%
Total 100% 100%
Preparation of xylem oil (i)
55 parts by weight of diisononyl adipate, 20 parts by weight of diethylene glycol monomethyl ether, 20 parts by weight of “Naphthezol 240” (manufactured by Shin Nippon Petrochemical Co., Ltd.), 1 part by weight of tebuconazole, 1 part by weight of propiconazole, An oil agent is prepared by adding 3 parts by weight of 2-phenyl-4-methylimidazole and dissolving it uniformly.

(Ii)
An oil agent is prepared in the same manner as in Production Example II (i) except that 55.9 parts by weight of diisononyl adipate, 2 parts by weight of 2-phenyl-4-methylimidazole, and 0.1 part by weight of clothianidin are used. .

Formulation Example-III
Emulsifying agent For wood and concrete (% is based on weight)
Nisseki Hyzol SAS-310 37%
Diethylene glycol monomethyl ether 25%
Rapeseed oil 10%
Narrow Acty N100 16%
IPBC 1%
Propiconazole 1%
2-phenyl-4-methylimidazole 10%
Total 100%
Preparation of emulsion for wood, concrete “Nisseki Hysol SAS-310” (manufactured by Nippon Petrochemical Co., Ltd.), 25 parts by weight of diethylene glycol monomethyl ether, and 10 parts by weight of rapeseed oil, 16 parts by weight (manufactured by Sanyo Chemical Co., Ltd.), 1 part by weight of 3-iodopropargyl-N-butylcarbamate (IPBC), 1 part by weight of propiconazole, and 10 parts by weight of 2-phenyl-4-methylimidazole Is added and dissolved uniformly to prepare an oil for emulsification.

Formulation Example-IV
Oil agent For heat insulation (% is based on weight)
ISOFOL14 61%
Diethylene glycol monomethyl ether 20%
Perlite (10μm) 8%
IPBC 1%
2-phenyl-4-methylimidazole 10%
Total 100%
Preparation of oil agent for heat insulating material 61 parts by weight of “ISOFOL 14” (manufactured by Condea Japan Co., Ltd.), 20 parts by weight of diethylene glycol monomethyl ether, 1 part by weight of 3-iodopropargyl-N-butylcarbamate (IPBC), 2 -Add 10 parts by weight of phenyl-4-methylimidazole, dissolve it uniformly, and mix and disperse 8 parts by weight of pearlite 10 μm (manufactured by Neoylite Kosan Co., Ltd.) to prepare an oil agent.

Claims (8)

Following formula (1)

(Wherein R ¹ , R ² , R ³ and R ⁴ are the same or different and represent a hydrogen atom or a hydrocarbon group which may have a substituent)
An imidazole compound represented by:
(A) a compound in which R ² is an aryl group, R ³ is an alkyl group, and R ¹ and R ⁴ are hydrogen atoms;
(B) a compound in which R ² is a hydrogen atom, R ¹ is an alkyl group, an alkenyl group, an aryl group or an aralkyl group, and R ³ and R ⁴ are hydrogen atoms, or
(C) Compound in which R ² is an alkyl group, R ¹ is a hydrogen atom, an alkyl group, an alkenyl group, an aryl group or an aralkyl group, and R ³ and R ⁴ are hydrogen atoms
Containing an anti-termite agent. The termite agent according to claim ¹ , wherein in formula (1), R ² is an alkyl group, and R ¹ , R ^3, and R ⁴ are hydrogen atoms. The imidazole compound represented by the formula (1) is 2-C _6-10 Aryl-4-C _1-4 The anti-termite agent according to claim 1, which is an alkylimidazole.   The anti-termite agent according to claim 1, which is used for treating xylem or soil.   The anti-termite agent according to claim 1, which is used as a bait agent.   A method for controlling or preventing termites by applying the anti-termite agent according to claim 1 to a treatment area or an object to be treated that can be damaged by termites. The method according to claim 6 , wherein the anti-termite agent according to claim 1 is applied to an object to be treated selected from soil and wood. The method according to claim 6 , wherein the anti-termite agent according to claim 1 is contacted or fed to termites.